# Our biggest point gambles | Frequent Miler on the Air Ep374 | 9-4-26

Page: https://stenobird.com/podcast/frequent-miler-on-the-air-598384/our-biggest-point-gambles-frequent-miler-on-the-air-ep374-9-4-26
Text version: https://stenobird.com/podcast/frequent-miler-on-the-air-598384/our-biggest-point-gambles-frequent-miler-on-the-air-ep374-9-4-26.md
Podcast: [Frequent Miler on the Air](https://stenobird.com/podcast/frequent-miler-on-the-air-598384)
Published: 2026-09-04T17:00:00+00:00
Episode link: https://voyascape.com/frequent-miler/our-biggest-point-gambles-frequent-miler-on-the-air-ep374-9-4-26
Audio file: https://episodes.captivate.fm/episode/c88b59d3-8653-413a-834b-4c0ed37c52e8.mp3
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JSON: https://stenobird.com/v1/public/podcasts/frequent-miler-on-the-air-598384/episodes/our-biggest-point-gambles-frequent-miler-on-the-air-ep374-9-4-26
Duration seconds: 3469

## Resource

This podcast episode is sponsored by Saily. Saily is an ESIM service app created by the security experts behind NordVPN. Instead of paying absurd daily rates to your home carrier or swapping SIM cards on arrival, Saily gives you flexible prepaid data plans in over 200 destinations worldwide. Download Saily from your app store and use our code FREQUENTMILER at checkout to get 15% off your first purchase. https://saily.com/frequentmiler On today's episode, we'll talk about why Air Canada to Hyatt 2-to-1 transfers can be a good deal, how we won big on a 240x deal, the 250x deal that got away, and much more. Our apologies for Nick's lower-quality audio this week! We're working to fix it! Our biggest point gambles Giant Mailbag (01:04) - Josh: Is the Hyatt/Aeroplan deal good for Canadians? Main Event: Our biggest point gambles (07:54) - When we took big risks to earn big miles... (08:04) - Nordstrom 36X (2012) (15:32) - Convert 90K SPG points into a 7 night Marriott stay + 120K Southwest points + Companion Pass for 2 years (2017) (19:43) - Marriott Travel Packages (2018) (23:40) - Iberia 90K (2018) (27:54) - Conservation International 240 AA miles per dollar (2021) (34:40) - Amex 20% transfer bonus to Hawaiian Airlines (2024) (39:28) - SAS: Fly 15 SkyTeam, earn 1M SAS Miles (2024) (44:50) - JetBlue 25/25 (2025) (48:42) - Kate Spade 250X via British Airways portal (2026) Subscribe and Follow Visit https://frequentmiler.com/subscribe/ to get updated on in-depth points and miles content like this, and don’t forget to like and follow us on social media. Music Credit – “Ocean Deep” by Annie Yoder Check out all of our other travel podcasts from around the world This podcast is part of the Voyascape Network, a collection of some of the world’s best travel podcasts. Explore more at…

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## Transcript

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